Factors governing orientation in metalation reactions. IV. The role of alkoxide in metalation reactions involving organosodium compounds

RA Benkeser, TF Crimmins, W Tong

Index: Benkeser,R.A. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 4366 - 4370

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Citation Number: 10

Abstract

Abstract: The metalation of t-butylbenzene with n-amylsodium, both in the presence and absence of sodium t-butoxide, was studied. The yield of the alkoxide metalation was much higher than the yield without alkoxide. A variable which affects isomer distribution, both in the presence or absence of alkoxide, is the amount of dimetalation which occurs, since the latter takes place principally at the expense of the mefa isomer. In the presence of ...